In recent years there has been a great deal of effort directed to the development of sulfonamides having herbicidal activity and several of these compounds have reached the stage of commercialization, i.e., chlorosulfuron and sulfometuron methyl. These compounds exhibit both preemergence and postemergence activity against undesirable vegetation and, in addition, have a low toxicity to mammals. The compounds of the prior art may be depicted as follows: ##STR1## wherein Ar is usually a benzene derivative and Ar' is usually a pyrimidine or symmetrical triazine derivative.
In addition, there are a number of other sulfonamide herbicides that have been commercialized, for example, methyl sulfanilylcarbamate; O,O-diisopropyl phosphorodithioate-S-ester with N-(2-mercaptoethyl)benzenesulfonamide; 3-isopropyl-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide; N-[2,4-dimethyl-5-[[(trifluoromethyl)sulfonyl]amino]phenyl]acetamide and 3,5-dinitro-N.sup.4, N.sup.4 -dipropylsulfanilamide.
It has now been found that novel compounds having the formula: ##STR2## wherein
Ar represents an aromatic or heteroaromatic ring chosen from among phenyl; 1- or 2-napthyl; 2-, 3- or 4-pyridyl; 2- or 3-thienyl; 2- or 3-furyl; 2-, 4-, or 5-thiazolyl; 2-, 4-, or 5-imidazolyl; 2-, 4-, or 5-oxazolyl; 3-, 4-, or 5-isothiazolyl; 3-, 4-, or 5-isoxazolyl; 3-, 4-, or 5-pyrazolyl; 2-benzthiazolyl; 2-benzoxazolyl; 2-benzimidazolyl: or 1-benztriazolyl; and Ar is unsubstituted except in the case of where Ar is phenyl or Ar is substituted with one to five substituents chosen from among C.sub.1 -C.sub.6 alkyl; benzyl; halo; C.sub.1 -C.sub.6 mono- or polyhaloalkyl; phenyl; phenyl substituted with one or more groups chosen from halo, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 haloalkyl; hydroxy; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 mono- or polyhaloalkoxy; phenoxy; phenoxy substituted with one or more groups chosen from halo, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 haloalkyl; 2-pyridyloxy; 2-pyridyloxy substituted with one or more groups chosen from halo, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 haloalkyl; amino; C.sub.1 -C.sub.6 alkylamino; C.sub.1 -C.sub.6 dialkylamino; nitro; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 polyhaloalkylthio; C.sub.1 -C.sub.6 alkylsulfinyl; C.sub.1 -C.sub.6 polyhaloalkylsulfinyl; C.sub.1 -C.sub.6 alkylsulfonyl; C.sub.1 -C.sub.6 polyhaloalkylsulfonyl; phenylthio; phenylthio substituted with one or more groups chosen from halo, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 haloalkyl; phenylsulfinyl; phenylsulfinyl substituted with one or more groups chosen from halo, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 haloalkyl; phenylsulfonyl; phenylsulfonyl substituted with one or more groups chosen from halo, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 haloalkyl; cyano; carboxyl; C.sub.1 -C.sub.10 alkoxycarbonyl; phenoxycarbonyl; phenoxycarbonyl substituted with one or more groups chosen from halo, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 haloalkyl; alkoxyalkoxycarbonyl wherein the number of carbons in the alkoxyalkoxy fragment ranges from 2-10 and the number of oxygens in the alkoxyalkoxy fragment ranges from 2-4; 2-pyridylmethoxycarbonyl; dialkylaminoalkoxycarbonyl wherein the number of carbons in the dialkylaminoalkoxy fragment ranges from 3-10 and the number of oxygens in the dialkylaminoalkoxy fragment is one; C.sub.3 -C.sub.6 alkenyloxycarbonyl; COON.dbd.C(R.sup.14)(R.sup.14 ) wherein each R.sup.14 independently represents hydrogen, C.sub.1 -C.sub.6 alkyl or phenyl; amino-, C.sub.1 -C.sub.6 alkylamino-, or di C.sub.1 -C.sub.6 alkylaminocarbonyl; C.sub.1 -C.sub.10 alkoxysulfonyl; C.sub.1 -C.sub.4 polyhaloalkoxysulfonyl; di C.sub.1 -C.sub.6 alkylaminosulfonyl; formyl; C.sub. 1 -C.sub.6 alkylcarbonyl; C.sub.1 -C.sub.6 mono- or polyhaloalkylcarbonyl; phenylcarbonyl; phenylcarbonyl substituted with one or more groups chosen from halo, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 haloalkyl; or C(R.sup.15)(R.sup.15)OR.sup.16 wherein each R.sup.15 independently represents hydrogen or C.sub.1 -C.sub.6 alkyl and R.sup.16 represents hydrogen, C.sub.1 -C.sub.6 alkyl, benzyl, phenylcarbonyl or C.sub.1 -C.sub.6 alkylcarbonyl (except in the cases of thio, sulfinyl, and sulfonyl substituents where if one of these substituents is present the other one to four Ar substituents may not be chosen from among the other two; oxycarbonyl substituents where the other one to four Ar substituents may not be chosen from among different oxycarbonyl substituents; or aminocarbonyl substituents where the other one to four Ar substituents may not be chosen from among different aminocarbonyl substituents); X, Y, and Z independently represent hydroxyl; carboxyl; hydrogen; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 mono- or polyhaloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 mono- or polyhaloalkoxy; amino, C.sub.1 -C.sub.4 alkylamino, or di C.sub.1 -C.sub.4 alkylamino; phenyl; phenyl substituted with one or more groups chosen from halo, nitro, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 mono- or polyhaloalkyl; C.sub.1 -C.sub.6 alkylthio; halo; or two adjacent substituents (i.e., X and Y or Y and Z) are joined together to form a five, six, or seven-membered saturated cyclic structure of carbon atoms or one said carbon atom of X,Y or Y,Z is replaced by a heteroatom chosen from among nitrogen, oxygen, or sulfur (i.e., X,Y or Y,Z is --(CH.sub.2).sub.n -- wherein n is 3, 4, or 5; or X,Y or Y,Z is --(CH.sub.2).sub.n --A--(CH.sub.2).sub.m -- wherein n is 0-4, the value of m is equal to the ring size minus (n+3) and A is NH, O, or S); and V is H or R and R represents C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.10 alkynyl, phenylalkyl, C.sub.2 -C.sub.10 alkanoyl, C.sub.1 -C.sub.10 alkoxycarbonyl, phenoxycarbonyl, di C.sub.1 -C.sub.6 alkylaminocarbonyl, C.sub.1 -C.sub.6 alkylsulfonyl, phenylsulfonyl, C.sub.1 -C.sub.10 alkoxythiocarbonyl or phenoxythiocarbonyl, wherein alkyl, alkenyl, alkynyl, and alkoxy in each instance is optionally substituted by halo and each phenyl moiety is optionally substituted by one or two groups selected from halo, nitro, C.sub.1 -C.sub.4 alkyl, or C.sub.1 -C.sub.4 haloalkyl; and, when V represents hydrogen, agriculturally acceptable salts thereof are useful pre- and post-emergence herbicides or intermediates for preparing herbicides.
Treatment of the locus of undesired vegetation or weeds with the novel compounds or with compositions containing herbicidally effective amounts of the novel compounds in admixture with one or more inert carriers can be used to obtain broad spectrum or selective weed control depending upon the specific compound and the amount applied. Broadleaf weeds are particularly susceptible to the compounds and control of undesirable vegetation in crops such as wheat, rice, corn, soybeans, and cotton can be achieved. Aquatic vegetation is controlled by the compounds.
In addition, certain novel tetrahydro derivatives of the compounds of general Formula I, which can be represented by Formula II ##STR3## wherein X, Y, A, V, and Ar as defined hereinabove and their agriculturally acceptable salts also exhibit herbicidal activity.
The invention further encompasses certain of the novel substituted triazolo[1,5-a]pyrimidine-2-sulfonyl chlorides and certain of the novel substituted anilines which are useful in preparing the compounds of Formulae I and II.